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Step 1
Preheat oven or toaster oven to 400F/200C. Cut both ends off the squash. stand it up on the cutting board, and cut into fourths lengthwise. Scrape out the seeds and stringy parts around the seeds.
Step 2
Spray a baking sheet with nonstick spray and arrange spaghetti squash cut side up. Drizzle a little olive oil onto the cut surface of each piece of squash, rub the oil around with your fingers, and sprinkle each one with a little Greek seasoning. Roast the squash for 50 minutes, or until it strings apart easily with a fork. (I like the roasted spaghetti squash, but you can cook the spaghetti squash in the Instant Pot or in a slow cooker if you prefer!)
Step 3
While the squash cooks, peel the cucumber in stripes, cut into fourths lengthwise, then cut the strips into pieces about 3/4 inch wide, and put in a bowl.
Step 4
Chop the red onion and green bell pepper into pieces a little smaller than the cucumber and add to the bowl.
Step 5
Cut Kalamata olives and cherry or grape tomatoes in half and add to the bowl. (If you're using fresh oregano, chop up about a tablespoon of that as well.)
Step 6
Crumble the Feta cheese and set aside.
Step 7
In a small bowl or glass measuring cup, mix together the lemon juice, red wine vinegar, dried Greek Oregano, and desired amount of fresh-ground black pepper. Whisk in the olive oil and set dressing aside.
Step 8
When the squash is done, let it cool enough to handle; then use a fork to scrape the spaghetti squash strands away from the skin. Discard the skin and divide the spaghetti squash between four serving bowls. (Or refrigerate some if you're not eating it all right away.)
Step 9
Stir the Greek salad ingredients to combine. Then add the dressing (and fresh Greek oregano if using) and stir until all the ingredients are coated with dressing. (It may seem like too much dressing, but you want enough that it will drip down on the squash.) Gently stir in the crumbled Feta.
Step 10
Spoon a generous amount of the Greek salad mixture over each bowl of spaghetti squash, making sure you get some of the dressing in each serving. Eat right away.
Step 11
The spaghetti squash will last a few days in the fridge. I would reheat in the microwave just enough to remove the chill. I don't usually like to refrigerate tomatoes, but the Greek salad mixture could be prepared in advance and tomatoes added when you eat the leftovers.